For over 50 years, Herb Caen wrote a daily newspaper column about San Francisco. Among Caen’s most frequent topics was Market Street, which he regularly traversed to and from work (at 5th and Mission) and to his various social meetings. I recently came across Herb Caen’s “San Francisco, City on Golden Hills,” which includes wonderful illustrations by the great Asian-American artist, Dong Kingman. Caen’s 1967 account of Market Street, is illuminating, and reminds us that the new “Twitter” payroll tax exemption follows a series of plans and false starts regarding Mid-Market going back more than forty years.

“Whenever I feel I’m getting out of touch with the city—a fear that haunts all newsmen—I take a long walk along Market Street. This is better therapy than a hot oil rub, picking up a twenty-four-point bridge hand, or flipping a cigarette butt at a cable car slot and watching it go in without touching the sides.

A few minutes on Market will convince anybody, even the oldest native, that he’ll never get to know San Francisco. it’s the street of broken dreams, of frozen screams, of strangers rubbing elbows—a main street a million miles away from the San Francisco the Convention & Visitors Bureau tries so desperately to portray in its magazine ads: the Tony Bennett city of tiny cable cars climbing to the stars that look down on seven-course dinners, nights at the opera, and all that, sort of kitchy-koo.

In many ways Market is the most sophisticated street in town, if by sophistication you mean weary, worldly, and aloof. Its warmth is its coldness: you’re alone, but so is everybody else. In a city that in too many ways is like a small town, it is blessedly impersonal. You can walk from Sixth to the Ferry without seeing anyone even vaguely familiar, and a foolish friendly smile gets exactly what it deserves: a darting glance on ‘the edge of suspicion.

Market is teeming with San Franciscans you’ll never get to know. It is quite clear that they don’t want to know you, either. Nothing is given, nothing is expected— a truly civilized arrangement.

Market Street is the city in all its desperate vitality and glorious vulgarity—the Alcatraz of streets. It’s there, but nobody knows what to do with it. Every traffic plan runs up against it and falls back, defeated. The dreamers talk vaguely of pedestrian malls and islands of shrubbery, but there is doubt even in the pretty drawings; they will end up in the files (or the wastebasket) along with a thousand other plans bravely titled, 'What to Do About Market Street.'

It is wide, long, stubborn, and unregenerate— a true brute of a street. A dead end with a life all its own.”

A tribute to the great San Francisco Chronicle columnist Herb Caen, who died in 1997, can be found here.